Best Leadership Books of All Time

Karl Stark and Bill Stewart are managing directors and co-founders of Avondale, a strategic advisory firm focused on growing companies. Avondale, based in Chicago, is a high-growth company itself and is a two-time Inc. 500 honoree.

The against-all-odds survival tale of explorer Sir Ernest Shackleton and his 27-member crew is one of the most timeless leadership allegories out there. When the 1914 Antarctic voyage got stuck for over a year in an ice floe, Shackleton's extraordinary positivity and decisiveness is said to have almost singlehandedly saved the lives of his entire crew. His ability to motivate and inspire in the face of bitter cold and extreme deprivation has been fodder for thousands of business school case studies.

Never Give In! The Best of Winston Churchill’s Speeches by Winston S. Churchill (2003)

This collection of speeches are a terrific reminder of Churchill’s ability to inspire. Curated by the legendary statesman’s grandson, these rousing addresses span Churchill’s career from World War I to his honorary induction as a US citizen in 1963—and teem with energy and charisma. Even in the face of grave uncertainty—an impending Nazi invasion, bombings in London—Churchill exuded resilience and courage. The speeches are also striking in their candidness. He had no speechwriters or spin-doctors.

Wooden on Leadership: How to Create a Winning Organization by John Wooden (2005)

Easily the most successful college basketball coach in history, 10-time NCAA champion John Wooden was beloved by UCLA players and fans as both a coach and mentor. His “Pyramid of Success,” a triangular diagram illustrating 25 behaviors he saw as critical to personal achievement, is widely cited by management consultants and teambuilders worldwide. Though Wooden authored seven leadership books, this one most pointedly applies to the workplace. Wooden offers both concrete tips—each chapter concludes with a bulleted list of actionable steps—and “big picture” inspiration.

Onward: How Starbucks Fought for Its Life Without Losing Its Soul by Howard Schultz (2011)

The charismatic billionaire's tale of how he helped Starbucks claw its way back to the top of the java-chain is engrossing on several levels. For one, the hits-and-misses Schultz recounts ring familiar to anyone with even a passing familiarity with the chain (breakfast sandwiches, anyone?) and provide an honest look at the pitfalls of trial and error. Schultz's own rise from a rough Brooklyn childhood to Fortune 500 CEO is a touching backstory.

Alive: The Story of the Andes Survivors by Piers Paul Read (1975)

This harrowing true story of how 16 men survived a deadly plane crash and endured ten weeks stranded in the Andes is a study in the human will to survive. With little food and no source of warmth, the survivors—all members of a Uruguayan rugby team who'd just witnessed the sudden death of at least a dozen of their closest friends—were forced to weigh agonizing decisions, including whether to split up and search for safety or turn to their deceased friends for food. It’s a remarkable tale of how humans can rise to the occasion when suddenly thrust into a leadership position.

Primal Leadership: Realizing the Power of Emotional Intelligence by Daniel Goleman (2002)

In this analytical take on managerial success, the psychologist credited with popularizing the concept of "emotional intelligence,” looks at its application to leadership. Through dozens of case studies, Goleman builds a convincing argument that the best leaders are—for lack of a better term—in touch with their feelings. Individuals with what he calls "resonance," the ability to channel emotions in a positive direction, are by and large the most effective and inspiring.

The Art of War by Sun Tzu (5th century B.C.)

Dozens of notable leaders from Napoleon and General MacArthur to Marc Benioff and Bill Belichick claim to draw inspiration from this ancient Chinese military manual. Comprised of 13 sections, each dedicated to a different aspect of battle strategy, The Art of War is packed with timeless insights into how to set goals and achieve them. The basic premise: that “strategy” isn’t so much a matter of list-making as it is preparation to react swiftly and appropriately to any situation that might come up.

The Prince by Niccolo Machiavelli (1532)

Although "Machiavellian" is not a trait one would ever profess to want in a boss, coach or head of state, the Italian philosopher's controversial treatise is nonetheless a timeless leadership reference book for understanding them. Machiavelli's infamous position on the value of being feared versus loved is in fact more nuanced than popular culture would lead you to believe. His reasoning on the merits of being loved versus feared versus hated is lucid and not necessarily malevolent. He argues above all that it's important not to be hated.

Questions of Character: Illuminating the Heart of Leadership Through Literature by Joseph L. Badaracco Jr. (2006)

What can literature’s greatest characters teach us about leadership? An infinite amount, according to Badaracco, whose literature course, “The Moral Leader,” is a popular draw at Harvard Business School. Common among nearly all the great works of literature is a central character facing a grave challenge. Think Antigone, Death of a Salesman’s Willy Loman or Things Fall Apart’s Okonkwo. Badaracco segments his book into eight different questions leaders commonly face and illustrates each one with a literary example. The result is a wise, and never pedantic, reflection on the challenges of leading and the perils of failing to do it well. —Devon Pendleton

Delivering Happiness: A Path to Profits, Passion and Purpose by Tony Hsieh (2009)

This fun-loving entrepreneur may be as well-known for his unconventional management principles as he is for his Zappos shoe empire. Tony Hsieh’s high-minded manifesto: The workplace can and should be a place where employees find personal fulfillment. To that end, Hsieh focuses on fostering happy, passionate, and communicative staffers. When set against the success story that is Zappos—where there’s a free Zappos library, and feel-good training seminars—it’s clear Hsieh is onto something.

Team of Rivals: The Political Genius of Abraham Lincoln by Doris Kearns Goodwin (2005)

When asked in a 2008 interview what one book he'd take to the White House if he could choose only one (besides the Bible) President Obama chose this one. President Lincoln's ability to unite, and his success bridging vastly divergent personalities and ideologies, is perhaps his single-most admired leadership trait. Pulitzer Prize-winning historian Kearns Goodwin illuminates Lincoln's keen understanding of human behavior by tracing his relationship with the political antagonists he chose for his cabinet. Ever humble, Lincoln chose to surround himself with ambitious, strong-willed personalities who were unafraid to challenge him.

On Becoming a Leader by Warren Bennis (1989)

This thought-provoking classic of business literature draws from hundreds of interviews to help answer the question: What is a good leader? Professor Bennis, a pioneer in leadership studies, casts his net wide, examining the psychological and philosophical attributes of thinkers, scientists, executives, and entertainers who all share an ability to unite people in a common purpose. Anyone looking for a comprehensive, well-researched, and actionable guide to being a better leader could not do better than Bennis' insightful tome.